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Anna’s Substack · Aug 21, 2026

Italy in Outfits

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Anna Porte · Anna’s Substack

Hi from Montreal! I’m back in the city with just a touch of post-vacation blues, which is always a sign of a great trip. And while I’m still dreaming of days in Italy—what better time for the usual packing debrief.

From the camera roll.. colours of Ischia!

When it comes to vacation dressing, I love the idea of going all out and putting on my very best looks, but the reality is, when I’m travelling I just want things to feel relaxed and easy. Of course I want to feel good in what I’m wearing, but mostly what I want is to not spend time on my outfit. I want to throw on something comfortable and weather-appropriate, and enjoy!! The whole point of vacation is not working or thinking very hard about anything—including my clothes.

The outfits in this letter are a reflection of that mentality—a combination of effortless pieces I’ve collected over the years and a few newer things I picked up earlier this summer. Things that made getting dressed feel easy, but that I still felt really good in.

Easy Outfits for Day and Night

I’ve tried pre-planning looks for trips in the past, and while it’s great in theory, I almost always abandon the plan in favour of dressing for my mood. Instead, I focus on putting together an edit of clothes and accessories that can easily be mixed and matched. Easy dresses and linen and cotton separates are key.

I lovee these pearl earrings. I get so much use out of them both on vacation and otherwise.

I’ve had this Deiji Studios dress for a few years now and it’s still one of my favourites. A go-to for running down to breakfast or a quick outing. They don’t seem to make it anymore, but this one gives the same energy.

Excuse the unruly hair, this photo was taken just minutes after emerging from truly one of the better massages of my life. I love this Riposo nightgown for vacation and it was the perfect thing to throw on to get to and from the spa. It reminds me of this Toteme dress—the cut is nearly identical!

Another Loretta Caponi number. Their pieces come at a higher price point, but they genuinely look and feel really special. Alternatively, Zara Home also really knows how to do a white embroidered dress that feels right for vacation.

Matteau is another favourite brands for warm-weather dressing. This dress is lovely and breezy and can just as easily be worn over a swimsuit to the beach as it can to dinner, as I’ve done here.

This is my third summer with this Faithfull dress. No longer available, but these two are similar.

I found the top at a thrift shop that my girlfriend brought me to in Brooklyn. It reminds me of this linen V-neck tank from 100% Capri. Wearing it with my favourite pair of linen pants.

Rewearing this very special Attersee dress I wore for my legal wedding last summer. Dressed down with a flat thong sandal for dinner in Positano.

Another good dress to throw on for breakfast.

Swim and Cover-Ups

This piece came into my closet earlier this spring. It makes for a beautiful cover-up, but I’ve also worn it in the city over the summer—really versatile. No lace detail, but a really pretty alternative nonetheless. This too!

Ironically (or embarrassingly), I’m now realizing that I wore a Da Adolfo x Staud headscarf to Da Adolfo.

Over the years, I’ve collected a few Eres swimsuits—they’re an investment but they’re incredibly well made and last forever. I’m wearing the Aquarelle here, which is my favourite style they make.

I always pack a sarong in my beach bag so that I don’t have to throw clothes on over a wet bathing suit on my way back to the room. Feels better to wrap a pareo around my waist instead.

Another oldie but goodie! Dôen dresses forever— these two are similar. Wearing the Aquarelle in white underneath, it’s the perfect swimsuit to pair with a sheer white dress.

The bathing suit came with a matching scrunchie which was much appreciated. This black one piece from the collection looks really good too.

This cover-up is an older Dôen nightgown, but I love to wear it over a swimsuit. Eres Mouna Bikini Top and Bottom underneath in a blue colourway from a few seasons ago— I love this green thats currently available.

If Only If’s Poppy strikes me as another nightgown that would work well as a cover up.

Toiletries, Skincare, and SPF

Sunscreen is essential on a summer vacation, of course. The Le Prunier is my everyday go-to and comes everywhere with me, but I also picked up two from Isdin from the spa at our hotel in Ischia. The texture of this Fusion Water Magic is genuinely impressive. I audibly wow-ed the first time I used it. Suuuper lightweight, almost serum-like. I also always love to have a spray for re-application while I’m out so I don’t have to touch my face (yes, I’m a bit neurotic when it comes to avoiding breakouts). For body, I tried this Moisturizing Sunscreen for the first time, which is lovely and feels really nice on the skin.

In terms of skincare, I kept it tight and brought the essentials for my everyday AM and PM routine (the first eight products linked here), a few of my favourite eye masks and some travel packs of these face towels (if you’re acne-prone I highly rec!).

For haircare, I also kept it pretty simple—pocket hairbrush, a wooden comb (which Zach and I share), Milk hair serum (also share), Air Dry Mousse, a few scrunchies, and clips in two different sizes.

I separate beauty products by category—sunscreens in this pouch (which then goes straight into my beach bag), skincare in this one, haircare in this, and makeup in this!

I think that about covers it, but if I missed anything, comment below or shoot me a DM!

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